Real-World Topics: Medicinal ChemistryArrietta ClaussInstructors often look for real-world topics that interest students when designing labs and preparing lectures. The chemistry associated with drugs is a fertile area, and the archives of the Journal can be a resource for interesting drug-related activities to enhance student learning.Clauss, Arrietta. J. Chem. Educ.2008, 85, 1657.

Molecules and Medicine (E. J. Corey, Barbara Czakó, and László Kürti)Robert E. BuntrockLooking for a book on common drugs and pharmaceuticals? On diseases and medical conditions? On pharmacology? In addition, do you need some background in chemistry to handle all of this information? If you want all of this, and in addition want it under one cover, then this is the book for you.Buntrock, Robert E. J. Chem. Educ.2008, 85, 1495.

Bioorganic Chemistry |

Drugs / Pharmaceuticals |

Molecular Properties / Structure |

Proteins / Peptides |

Synthesis |

Toxicology

Molecular Models of Real and Mock Illicit Drugs from a Forensic Chemistry ActivityWilliam F. ColemanThe Featured Molecules for this month have been drawn from a forensic chemistry exercise in which model compounds are used to simulate the behavior of various drugs in a series of chemical tests. The compounds considered include chlorpromazine (Thorazine) and phenothiazine, both involved in the manufacture of antipsychotic drugs.Coleman, William F. J. Chem. Educ.2008, 85, 880.

Nature's Way To Make the LantibioticsHeather A. Relyea and Wilfred A. van der DonkThis article focuses on one class of antimicrobial compounds, the lantibiotics, and discusses their biosynthetic pathways as well as their molecular mode of action. In the course of the review, the meaning of the terms regio-, chemo-, and stereoselectivity are discussed.Relyea, Heather A.; van der Donk, Wilfred A. J. Chem. Educ.2006, 83, 1769.

Applications of Chemistry |

Bioorganic Chemistry |

Biotechnology |

Biosynthesis |

Catalysis |

Drugs / Pharmaceuticals |

Proteins / Peptides

An Introduction to UV–Vis Spectroscopy Using SunscreensHarriet P. Moeur, Andrew Zanella, and Thomas PoonTwo commercially available lotions that utilize only one active ingredient as a sunscreen were used to develop a general chemistry laboratory experiment involving the quantitative determination of the active component in each lotion by UVvis spectroscopy.Moeur, Harriet P.; Zanella, Andrew; Poon, Thomas. J. Chem. Educ.2006, 83, 769.

Drugs / Pharmaceuticals |

Fluorescence Spectroscopy |

Spectroscopy |

UV-Vis Spectroscopy

The Discovery and Development of CisplatinRebecca A. Alderden, Matthew D. Hall, and Trevor W. HambleyCisplatin is currently one of the most widely used anticancer drugs in the world. The unlikely events surrounding the discovery of its anticancer activity, subsequent introduction into the clinic, and the continuing research into platinum compounds is the subject of this review.Alderden, Rebecca A.; Hall, Matthew D.; Hambley, Trevor W. J. Chem. Educ.2006, 83, 728.

Bioinorganic Chemistry |

Coordination Compounds |

Drugs / Pharmaceuticals |

Medicinal Chemistry |

Metallic Bonding |

Oxidation State |

Synthesis

Presumptive and Confirmatory Drug TestsCraig AndersonTests for illegal drugs were performed on unknowns obtained from over-the-counter cold medicines. Substances that tested positive for the qualitative Marquis color test were found to be false positives for illegal substances, while scopolamine hydrochloride shows a false positive for cocaine hydrochloride with the cobalt thiocyanate reagent. Anderson, Craig. J. Chem. Educ.2005, 82, 1809.

Stoichiometry of Calcium MedicinesGabriel PintoCalcium supplements provide an excellent context in which to review most of the core content of general chemistry, namely, stoichiometry, concentration units, hydration of salts, inorganic and organic salts, physiological importance of elements, resonance in ions, geometry of polyatomic ions, and isomerism.Pinto, Gabriel. J. Chem. Educ.2005, 82, 1509.

Stoichiometry |

Applications of Chemistry |

Drugs / Pharmaceuticals |

Medicinal Chemistry

Based on a True Story: Using Movies as Source Material for General Chemistry ReportsMark A. Griep and Marjorie L. MikasenPresents a list of one dozen, highly rated movies in which the focus is either a scientist's chemical research or the societal impact of some chemical compound. The method by which two of these movies were used as source material for a written report in a general chemistry course is described.Griep, Mark A.; Mikasen, Marjorie L. J. Chem. Educ.2005, 82, 1501.

Medicinal Chemistry |

Women in Chemistry |

Applications of Chemistry |

Drugs / Pharmaceuticals |

Industrial Chemistry |

Nonmajor Courses |

Nuclear / Radiochemistry

A Supramolecular Approach to Medicinal Chemistry: Medicine Beyond the MoleculeDavid K. SmithThis article emphasizes a conceptual view of medicinal chemistry, which has important implications for the future, as the supramolecular approach to medicinal-chemistry products outlined here is rapidly allowing nanotechnology to converge with medicine. In particular, this article discusses recent developments including the rational design of drugs such as Relenza and Tamiflu, the mode of action of vancomycin, and the mechanism by which bacteria develop resistance, drug delivery using cyclodextrins, and the importance of supramolecular chemistry in understanding protein aggregation diseases such as Alzheimer's and CreutzfieldJacob. Smith, David K. J. Chem. Educ.2005, 82, 393.

Drugs / Pharmaceuticals |

Noncovalent Interactions |

Medicinal Chemistry |

Nanotechnology |

Proteins / Peptides

Using Clinical Cases To Teach General ChemistryBrahmadeo Dewprashad, Charles Kosky, Geraldine S. Vaz, and Charlotte L. MartinThis article describes how a fact-based clinical case was effectively used to motivate and enrich the classroom experience and review many of the concepts covered in general chemistry. The case involves an elderly patient who was brought to the emergency room. The results of his physical examination and laboratory analysis of his blood are presented. The students, in peer-led groups, work through the chemical principles involved in the doctor's diagnosis and treatment options for the patient. The article describes the case study, instructors' observations, and students' perception of the activity. Dewprashad, Brahmadeo; Kosky, Charles; Vaz, Geraldine S.; Martin, Charlotte L. J. Chem. Educ.2004, 81, 1471.

A General Chemistry Laboratory Theme: Spectroscopic Analysis of AspirinHouston Byrd and Stephen E. O’DonnellA laboratory sequence designed for introductory chemistry students that focusses on the synthesis and spectroscopic (IR and NMR) and chromatographic (HPLC) analysis of aspirin as an alternative to traditional general chemistry laboratories.Byrd, Houston; O’Donnell, Stephen E. J. Chem. Educ.2003, 80, 174.

Synthesis of the Sweetener Dulcin from the Analgesic TylenolBrian D. Williams, Birute Williams, and Louise RodinoA sequence suitable for the synthesis of the sweetener dulcin from the analgesic acetaminophen. The analgesic phenacetin is isolated during the synthesis as an intermediate and consequently the experiment can be adopted as a multistep synthesis or as either of two single-period transformations.Williams, Brian D.; Williams, Birute; Rodino, Louise. J. Chem. Educ.2000, 77, 357.

Experiments with AspirinLonda L. Borer and Edward BarryExperiments include (i) synthesis, purification, and characterization of aspirin by mp and TLC, (ii) percentage composition of a commercial aspirin tablet by titration, (iii) kinetics of the hydrolysis of aspirin to salicylic acid under various conditions, (iv) synthesis and characterization of copper(II) aspirinate and copper(II) salicylate, and (v) reaction of copper(II) aspirinate in aqueous solution. Borer, Londa L.; Barry, Edward. J. Chem. Educ.2000, 77, 354.

Synthesis |

Kinetics |

Drugs / Pharmaceuticals |

Medicinal Chemistry |

Aromatic Compounds

A Brine Shrimp Bioassay for Measuring Toxicity and Remediation of ChemicalsMarya LiebermanA bioassay using brine shrimp was adapted to measure the toxicity of household chemicals. One project is described in which students collect dose-response curves for seven commercial flea-killing products. Next, groups of students researched the insecticidal ingredients of the flea products. On the basis of the structures of the active ingredients, they chose remediation methods to make the flea product less toxic to brine shrimp; procedures included copper-catalyzed hydrolysis, adsorption onto activated charcoal, bleach treatment, and photodegradation.Lieberman, Marya. J. Chem. Educ.1999, 76, 1689.

Drugs / Pharmaceuticals |

Medicinal Chemistry |

Nonmajor Courses |

Toxicology

An Acid-Base Chemistry Example: Conversion of NicotineJohn H. SummerfieldThe current government interest in nicotine conversion by cigarette companies provides an example of acid-base chemistry that can be explained to students in the second semester of general chemistry.Summerfield, John H. J. Chem. Educ.1999, 76, 1397.

Acids / Bases |

Drugs / Pharmaceuticals |

Equilibrium

Exploring the Ocean- Stating the Case for ChemistryPaul J. ScheuerSalinity measurements and carbonate-bicarbonate equilibria used to be the only topics studied under what was known as "marine chemistry". But in the past few decades organic chemists have changed this situation profoundly by exploring the diverse fauna and flora of coral reefs and the ocean floor.Scheuer, Paul J. J. Chem. Educ.1999, 76, 1075.

Synthesis of Aspirin: A General Chemistry ExperimentJohn A. Olmsted IIIAn experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer.Olmsted, John A., III. J. Chem. Educ.1998, 75, 1261.

Drugs / Pharmaceuticals |

Medicinal Chemistry |

Mechanisms of Reactions |

Aromatic Compounds |

Carboxylic Acids |

Aldehydes / Ketones

The Art and Science of Organic and Natural Products SynthesisK. C. Nicolaou, E. J. Sorensen, and N. WinssingerIn this article, the history of the art and science of organic and natural products synthesis is briefly reviewed and the state of the art is discussed. The impact of this discipline on biology and medicine is amply demonstrated with examples, and projections for future developments in the field are made. Nicolaou, K. C.; Sorensen, E. J.; Winssinger, N. J. Chem. Educ.1998, 75, 1225.

Natural Products |

Synthesis |

Medicinal Chemistry |

Applications of Chemistry |

Drugs / Pharmaceuticals

An Efficient Microscale Procedure for the Synthesis of AspirinSangeeta Pandita and Samta GoyalWe have found that aspirin can be synthesized on microscale by a simple and efficient procedure that eliminates the heating step employed in literature procedures and gives a pure, ferric-negative product (no purple color with alcoholic ferric chloride solution).Pandita, Sangeeta; Goyal, Samta. J. Chem. Educ.1998, 75, 770.

Microscale Lab |

Synthesis |

Drugs / Pharmaceuticals

A Study of the pH of Sweat for Horses: A Student-Devised Study by Science and Health Science MajorsJohn Tierney, Lori Peacock, Erica Sorkin, and Susan WareThis article describes the results obtained when the pH for horse sweat was measured. Comparisons with the studies on humans are also noted. The pH of perspiration produced by mares and gelding was measured under controlled conditions and found to be between 6.7 to 10. Tierney, John; Peacock, Lori; Sorkin, Erica; Ware, Susan. J. Chem. Educ.1997, 74, 1135.

Learning Theories |

Acids / Bases |

Drugs / Pharmaceuticals |

Undergraduate Research

The Thermodynamics of Drunk DrivingRobert Q. ThompsonBiological, chemical, and instrumental variables are described along with their contributions to the overall uncertainty in the value of BrAC/BAC. Thompson, Robert Q. J. Chem. Educ.1997, 74, 532.

Thermodynamics |

Nonmajor Courses |

Forensic Chemistry |

Drugs / Pharmaceuticals |

Applications of Chemistry

Reports from Other Journals: Gleanings from Scientific AmericanPaul F. SchatzScientific American provides a rich resource of background and general interest material for topics of chemical interest that can be used to supplement and enhance chemistry lecture and laboratory courses.Schatz, Paul F. J. Chem. Educ.1996, 73, A234.

Drugs / Pharmaceuticals |

Nuclear / Radiochemistry |

Calorimetry / Thermochemistry |

Laboratory Equipment / Apparatus |

Applications of Chemistry |

Consumer Chemistry |

Laboratory Management

A Simulated Growth Hormone AnalysisMary HarrisGrowth hormone is a drug that is sometimes abused by amateur or professional athletes for performance-enhancement. This laboratory is a semi-microscale simulation analysis of a sample of "urine" to detect proteins of two very different molecular weights.Harris, Mary. J. Chem. Educ.1996, 73, 735.

Chemistry and detective fiction: An interdisciplinary program for the nonscience majorLabianca, Dominick A.; Reeves, William J.Drugs, poisons, and detective fiction offer many possibilities for science/literature integration. The interdisciplinary teaching methods described in this note can address the problem of the alienation harbored by many non-majors toward science and can certainly contribute to a reversal of negative attitudes and to an increased interest in science beyond the formal classroom setting.Labianca, Dominick A.; Reeves, William J. J. Chem. Educ.1981, 58, 683.

Separation of an APC mixture. A quantitative analysis experimentHaddad, Paul; Rasmussen, MalcolmIn this paper the well known technique of pH, controlled extractive separation of a mixture of an acidic, basic, and neutral organic substance has been applied to separation and analysis of a mixture of the drugs aspirin, caffeine, and phenacetin.Haddad, Paul; Rasmussen, Malcolm J. Chem. Educ.1976, 53, 731.

An interdisciplinary approach to science and literatureLabianca, Dominick A.; Reeves, William J.Describes a literature course that concentrates on readings concerned with certain aspects of drug use and a science course that analyzes the problems associated with such drug intake.Labianca, Dominick A.; Reeves, William J. J. Chem. Educ.1975, 52, 66.

The thin-layer chromatography of drugs. A laboratory experimentNeman, R. L.Students are introduced to thin layer chromatography, are provided samples known to contain alkaloids and barbiturates, separate the mixtures using tlc, determine the components of their unknowns, and calculate Rf values for the components.Neman, R. L. J. Chem. Educ.1972, 49, 834.